Should he stay or should he go? Why a contract extension at Milan makes the most sense for USMNT star Christian Pulisic

To be clear, calling Pulisic's time in London unsuccessful would be wildly unfair. He won a Champions League there, and you can't reach higher highs than that. Pulisic wasn't a bystander on that team, either; he was an active participant. It was his semifinal goal against the mighty Real Madrid that helped lift the Blues into that final to begin with.

Still, there were plenty of lessons learned from Pulisic's time in blue. Chief among them? The importance of support.

Pulisic never really had that at Chelsea, where his legs were seemingly cut out from under him before he ever even kicked a ball. He signed during the Maurizio Sarri era, but the Italian was gone before Pulisic even arrived. Frank Lampard never really leaned on him. Thomas Tuchel, despite the Borussia Dortmund links between the two, didn't really unleash the American either.

A series of untimely injuries played their part, no doubt, but, even when healthy, Pulisic never had the full trust of his coaches or the fanbase at large. That weighs on a player, and Pulisic has admitted it took a toll on him. Outsiders saw it, too.

“I think he has got more trust in his game, more confidence," former teammate Olivier Giroud told CBS after playing with Pulisic at both Chelsea and Milan. "He plays with more freedom and he’s playing every single game. He’s a very important player for Milan. At Chelsea, he was in competition with so many wingers."

With Milan, Pulisic has established himself as THE guy. There's a reason those fans cheered for him above everyone else, after all.

It started last season, when Pulisic put up 12 goals and eight assists in Serie A, second on the team in both. This season, Pulisic has generally been even better, stepping up in big moments in both the league and Champions League.

Though he's currently nursing a calf injury that will keep him out until early 2025, as things stand, Pulisic leads Milan with five goals and he's tied with Leao on the assist leaderboard with four. You can add in Champions League success as well, with Pulisic putting in big shifts against Liverpool and Real Madrid when the lights were brightest.

All of this is coming despite what has otherwise been a frustrating season by Milan standards. The Rosonerri sit eighth in Serie A, having dropped far too many points. As a result, head coach Paulo Fonseca is under fire, as are the rest of Milan's top stars as the fans demand that the Serie A giants turn things around.

Pulisic, though, is not under the same pressure. Even the notoriously-prickly Zlatan Ibrahimovic has showered him with praise, calling for Pulisic to accept his place as the face of the team for both club and country.

"He is known for being 'Captain America', but he doesn’t like to be 'Captain America'. He doesn’t maybe see himself like a superhero," Ibrahimovic said in the new Pulisic documentary on Paramount+. "He is playing low profile and with his feet on the ground. But you are 'Captain America', I don’t give a sh*t what you say, you are. If that is more pressure on you, I don’t care. It is his own fault - if you weren’t so good, we wouldn’t ask anything from you."

With success, though, comes attention.

You should always be suspect about reading too much into transfer rumors. They are just rumors, after all. Still, if your name is swirling, it's because somebody, somewhere is expressing interest. When a player's name is out there, change is possible.

With his success, and Milan's struggles, speculation over Pulisic's future increased. Liverpool and Manchester United were among the clubs reportedly interested. The Reds could be looking for a new star if a new contract for their current one, Mohammed Salah, doesn't come to fruition. Manchester United - well, they can use all the help they can get right now.

West Ham have been linked, too, but, realistically, that would be a step down from Milan. Despite the allure of the Premier League, and the financial power, Milan is still a top club, while the Hammers are languishing below midtable. Premier League money or no Premier League money, they are not the same.

Are there any options that could tempt Pulisic? Realistically, how many clubs out there would even make sense to consider, given his success with Milan?

Pulisic will know this more than most: the grass isn't always greener in the Premier League. The money may be there, but you really can't put a price on comfort, can you?

A move to Liverpool could make sense for Pulisic, especially considering the club was linked to him all throughout Jurgen Klopp's tenure. This is a new era, though, and that brings no guarantees. One of Liverpool's biggest strengths at the moment is the club's depth in attack, which features Salah, Luis Diaz, Diogo Jota, Cody Gakpo, Darwin Nunez and Federico Chiesa. Even with a potential Salah departure, there are no guarantees there.

Manchester United? Very few have stepped into Old Trafford and gotten better in recent years. The club has struggled at every level, and that has trickled down to the field, where expectations have overwhelmed and overshadowed those who wear that extremely heavy red shirt every week.

Realistically, how many clubs in the world would be a step up from Milan? You can write off Chelsea - he isn't going back there. Manchester City and Arsenal, sure. Bayern Munich, sure. Maybe PSG if you want to win something. Both of the Spanish giants, of course, although both Real Madrid and Barcelona look set in the wing positions for years to come.

Pulisic has found a home with the greenest of grass, all things considered. He's landed at a huge club that supports him, on and off the field. Why give that up? Pulisic seems to understand that as he reportedly moves closer to putting pen to paper.

Even before his scorching start to the season, Pulisic spent parts of the summer talking up just how happy he is in Italy. He told the Bob Does Sports YouTube channel: "I’m loving Italy, Italy has been… dude it has changed my career around. Just the club as well, Milan has been just so enjoyable. The fans, the stadium… you guys got to get out to San Siro. Our stadium is just… I’ve never seen anything like it man. I live right by Lake Como, Milan, everything’s right there, Switzerland. You’re close to everything."

That's the off-field, and that is important. On the field, he's feeling the passion, too. A player's happiness is often a combination of off-field comfort and on-field success. In Milan, Pulisic is experiencing the best of both - at least for now.

“It’s not to say it’s easier now (at Milan) than it was with Chelsea, but there was a time in Chelsea where I felt on top of the world and I was playing great and that confidence and that no-fear mentality was easy to have," he said in the documentary. "And there was also a time when that was extremely difficult because I wasn’t getting the time. I felt pressure that I needed to do more when I did get on the pitch in some kind of way.

"Now, I’m in a really good head space where I feel quite confident. I feel a lot of trust from the club in a lot of ways.”

Pulisic looks set to respond to that by placing his own trust back in the club. Signing a new deal is a big commitment, one that would see him spend at least a few of his prime years representing the red and black of Milan. The club showed faith in him when he was at a lower point. Now that he's soaring, a new contract would be a show of faith from his side, as well, particularly with the club struggling.

The USMNT star will have thought long and hard about that. He'll have leaned on his past experience and his future expectations, too. And, if he decides that the best place for him is Milan, who can blame him? He's playing his best game, and the fans and club are on his side. What more could you ever want?